Out Gambitted / Film

• In Adventure In Kigan Castle, Osami is arrested after he's mistaken for a spy trying to kill the king of Kigan Castle, and is thrown in the dungeon to be executed. Granny the Old Witch tries to take advantage of this. She disguises herself as the queen, and visits Osami in his cell to try and make him join forces with her. However, Hermit the Old Wizard, Granny's sworn enemy, has already put Osami under a sleeping spell so that Granny can't talk to him.
• In Batman & Robin Poison Ivy spends most of the film seducing the title duo, turning them against each other and trying to kill them with her kiss. She eventually gets Robin alone and reveals what Freeze's plan is, in exchange for a kiss from 'her lover for luck'. Robin keeps the deal and kisses her but doesn't die thanks to wearing a rubber lip, stopping her poison. Unfortunately, he didn't expect her to shove him from her throne into her pond and try to have her plants drown him instead. Even more unfortunately for Ivy, Barbara shows up as Batgirl, and not only saves him, but also provides Batman with the key to destroying Ivy's lie to Freeze about his wife.
• Batman Returns: The Penguin orchestrates a crime wave to make the people of Gotham lose faith in the current administration. He has one of his mooks abduct the Mayor's infant child in broad daylight, only to show up himself and "rescue" it. He wins over the people's sympathies with his pitiful life story. He frames Batman for murder, and uses a remote controlled Batmobile to cut a path of destruction, making it seem as if Batman had finally snapped. All to instigate a recall election and get himself elected Mayor. But he didn't count on the Goddamned Batman having a disk drive in his Cool Car to record the Penguin's rants and broadcast them at his next speech:
  The Penguin: You gotta admit, I've played this stinking city like a harp from Hell!
• Batman: The Movie features multiples layers of this. The Penguin dons a Paper-Thin Disguise and tries to convince Batman and Robin that he's Commodore Shmidlab. Batman and Robin take him to the Batcave so they can prove that he's the Penguin and arrest him — once inside the Batcave, Penguin re-hydrates the mooks he's carrying (don't ask) and orders them to attack, which was his plan all along. However, the tragic demise (again, don't ask) of these same mooks apparently convinces Batman that Penguin really is Commodore Schmidlab — but as Batman and Robin are escorting him out of the Batcave, Penguin gasses both of them and steals the Batmobile. As soon as Penguin is out of sight, Batman and Robin wake up (they were faking unconsciousness, having taken an anti-knockout gas pill beforehand) and follow the Batmobile's homing beacon right back to the Penguin's lair.
• Bullet Train: The Prince controls The Father throughout the movie with a Dead Man's Switch on his son, who is currently in a coma in a hospital; if The Prince doesn't call her man every ten minutes, or fails to answer when he calls, the man will kill the son. When The Elder (The Father's father) shows up and interrogates her, he causes The Prince to miss a call. She mocks him that after everything that happened, his grandson is dead, and we get a shot of the assassin entering the hospital room. The Elder just smirks and says "My grandson was pushed off a building. Did you actually believe I would leave him unguarded?" Cut to a seemingly random nurse who had been in the background of previous scenes killing the assassin before he can touch the grandson.
• Circle:
  • When the room decides to force a universal tie in an attempt to cheat the game, one person secretly switches his vote to kill Pregnant Lady. Another astute person notices this, and switches his vote to that guy so he'll be trapped in a tie with Pregnant Lady. Of course, the room chooses to save her over him.
  • When the cast is whittled down to less than ten people, Eric manages to outmaneuver Bearded Man twice in a row. First, by observing that the Quiet Man never votes, he agrees to a deal to trade the Fake Wife for the Little Girl, voting in an order he knows would default to a majority for Fake Wife. Then, he makes up a story about the Quiet Man being untouchable and suggests voting for him, so that Bearded Man will waste his vote on Quiet Man and get eliminated himself.
• In Diamonds Are Forever, Shady Tree gets James Bond out of the retort with the intent to question him about where he hid the real diamonds. Neither he nor Morton Slumber counted on Bond having leverage against them to the tune of 50 grand (courtesy of Tiffany Case):
  James Bond: You wouldn't burn up 50,000 real dollars, would you? [...] You bring me the real money, and I'll bring you the real diamonds.
• In Diggstown, Bruce Dern gets out-gambitted by James Woods in an overtly crooked boxing wager. Realizing that he'd been bested by a superior conman, Dern shrugs and says, "You beat me fair and square!"
• The ending of Dirty Rotten Scoundrels has both male leads be out-conned by the woman they thought was their mark.
• Happens quite often in Drunken Master. In one instance, Jackie Chan's character has to scoop water from a bucket with teacups to fill another bucket while hanging upside down. When he notices his mentor is taking s nap, he quietly gets down, quickly fills the bucket with a much larger pan and then splashes waster on himself to make it as he's sweaty and tired. However, the napping teacher is one step ahead and when Jackie's character announces he's finished, the teacher hands him two extremely tiny teacups and tells him to do everything in reverse.
• Equilibrium. DuPont uses John Preston as an Unwitting Pawn in his scheme to expose the Resistance, but underestimates the latter's ability to strategically kill all of his mooks. Despite being the same person who decided to piss off a First Class Grammaton Cleric, who is a skilled master of plenty of deadly weapons and Gun Kata. Meaning he's made another fatal error where he specifically mentioned previously that someone who is a master of the latter is an adversary not to be taken lightly.
• Flightplan (2005): The villains' plans relied on them framing Kyle Pratt as the one who was taking the plan hostage and creating a mass disturbance by 'faking' a mental breakdown about her deceased daughter having been taken onto the plan, but once Kyle works out what's going on, she takes advantage of the fact that everyone else thinks she's the criminal to act as a genuine hijacker so that she can follow up a new lead until she can find her daughter.
• The finale of Hunting Humans is just one borderline ludicrous example of this after another. Let's see:
  • Serial Killer A goes to the home of the detective that Serial Killer B hired to keep tabs on him, and kills him. Serial Killer B (revealed to be the detective that Serial Killer A hired to keep an eye on Serial Killer B's detective) shows up to ambush him.
  • Serial Killer A reveals the detective isn't really dead, and that he hired him to his side.
  • Serial Killer B reveals that he knew Serial Killer A would try to bribe the detective to his side, so he offered him $5,000 on top of whatever Serial Killer A offered him to remain loyal.
  • Serial Killer A then reveals that he hacked into the detective's accounts and took all his money, and that the only way he can get it back is if Serial Killer A remains alive. After Serial Killer B kills the detective, Serial Killer A states he didn't take the money, he just made it look like he did.
  • Serial Killer A reveals he has an ally outside ready to snipe Serial Killer B at his command.
  • Serial Killer B manages to get outside, and into a wooded area, and when Serial Killer A follows him, Serial Killer B reveals that years of training have made him a fighting machine capable of countering everything that Serial Killer A throws at him.
  • Serial Killer A kills him using one of eighteen guns he had hidden in the forest, knowing the Serial Killer B would come to the detective's house, and that their battle might take them outside.
• How Jackie finishes her scheme in Jackie Brown. The cops want her to turn informant so she can help bring down her boss Ordell, a notorious Arms Dealer but Ordell has a nasty habit of killing people who turn informant (and has already attempted to do so before she pulled a gun on him). Ordell wants her to continue her money smuggling as an air stewardess, but if she does so the cops will just throw her ass in jail. So, instead, she understates how much money Ordell wants her to traffic for her to the cops, takes the majority for herself and, when Ordell realizes what she's done, gets the cops to wait for him at her apartment then get him killed with a single sentence — "He's got a gun!".
• In Jupiter Ascending, Balem and Titus spend most of the movie sending more guards or bribing more mercenaries to bring them Jupiter. Kalique buys out two of Balem's mercenaries so that she sees Jupiter first, and is nothing but polite and kind to her. The result is that Titus is under investigation by the Aegis and Balem is dead, while Kalique is alive and well to take control of the company, exactly as she wanted.
• Maverick. Bret and Zane out-gambit everyone who is trying to out-gambit them, and are topped themselves by Annabelle, who doesn't go ahead with some complicated con but instead just waits until all hell calms down, walks in on them while they are taking a bath with a gun in hand, takes the money and leaves. They don't mind — they think it's all a game and the fun will be in getting the money back from her. Plus Bret anticipated something of the kind and stashed half the money in his boots.
• Sands of Once Upon a Time in Mexico wanted druglord Barillo and General Marquez killed after allowing them to kill the President of Mexico in exchange for a pile of money. He gets Out-Gambitted on both sides, first when the Mariachi and his crew decide to fight for the President instead of letting him die, and when Ajedrez, a key player in his scheme, turns out not only to be a mole for Barillo, but also his daughter.
• Rock 'n' Roll High School marks possibly the only time where one gambit (Riff Randall waiting for three days to be first in line to get tickets to the Ramones concert and getting a hundred tickets for her friends and her music teacher) is Out-Gambitted by another gambit (Mrs. Togar donating her ticket and her best friend's ticket to charity), which is then Out-Gambitted by the Gambit Roulette that was Riff Randall's knowledge of the Ramones getting her and her best friend a free ticket each to the same concert. Riff's words to Mrs. Togar? "Screw you, Mrs. Togar, we made it to the concert anyway!"
• In The Silent Partner Cullen does this repeatedly to Reikle. Almost all of Reikle's attempts to get Cullen to fork over the money get him arrested or inconvenienced; when he finally pushed Cullen to far by murdering Elaine, he sets up Reikle to be killed.
• The plotters in The Spanish Prisoner had a multi-layered plan to get ahold of the process and leave Joe to take the fall. In the end the Feds were watching them the entire time and were just letting them proceed to gather evidence.
• In Spider-Man 3, Spider-Man is framed for a bank robbery thanks to Eddie Brock Jr. As it turns out, there never was a bank robbery the day earlier, and Brock's plan to get the office job at the Daily Bugle would've succeeded if Peter Parker hadn't recognized the photo from a previous photo of Spider-Man returning stolen loot to the bank (not to mention that Peter Parker had very good reason to be 100% certain that Spider-Man had never robbed any bank) and made sure Brock's scam was revealed to J. Jonah Jameson. In a later scene, Parker takes Brock's place in the office.
• Star Trek II: The Wrath of Khan: How Admiral Kirk was able to outwit Khan and escape from being marooned inside the Regula planetoid. Khan had left Captain Terrell and Commander Chekov behind to spring a trap on Kirk, while Kirk was able to determine exactly how long it would take to restore main power and rescue the landing party, leading Khan to believe it would take days instead of hours. Once the trap failed to kill Kirk, he made damn sure to convince Khan of his helplessness, counting on Khan to continue his pursuit of the Enterprise knowing that he could come back to finish Kirk at his leisure.
• Star Trek Into Darkness: How Spock defeats Khan, by allowing the latter to retrieve the armed torpedoes he thought contained his crewmates.
• Wild Things essentially consists of this trope and Fanservice.